MiMeDB: Showing metabocard for D-glucarate (MMDBc0054431)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:12:01 UTC

Update Date

2024-10-10 00:02:25 UTC

Metabolite ID

MMDBc0054431

Metabolite Identification

Common Name

D-glucarate

Description

Glucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. D-glucaric acid is found in fruits, vegetables, and mammals. The highest concentrations of glucaric acid are found in grapefruits, apples, oranges, and cruciferous vegetables (PMID: 18772850 ). Glucaric acid is produced through the oxidation of glucose. Cytochrome P450 is thought to be responsible for the production of D-glucaric acid in vivo (PMID: 3779687 ). In mammals, D-glucaric acid and D-glucaro-l,4-lactone are also known end-products of the D-glucuronic acid pathway (PMID: 18772850 ). Glucaric is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 9101079 ). D-Glucaric acid has a potential use as a building block for a number of polymers, including new nylons and hyperbranched polyesters. D-glucaric acid produced from D-glucose has been successfully utilized to produce a hydroxylated nylon.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-(+)-Saccharic acid	ChEBI
D-Glucosaccharic acid	ChEBI
D-Saccharic acid	ChEBI
L-Gularic acid	ChEBI
Saccharic acid	ChEBI
D-Glucaric acid	Kegg
Glucarate	Kegg
D-(+)-Saccharate	Generator
D-Glucosaccharate	Generator
D-Saccharate	Generator
L-Gularate	Generator
Saccharate	Generator
D-Glucarate	Generator
Acid, saccharic	MeSH
Anhydrous calcium glucarate	MeSH
Anhydrous calcium saccharate	MeSH
Calcium glucarate	MeSH
Calcium glucarate, anhydrous	MeSH
Calcium saccharate	MeSH
Calcium saccharate anhydrous	MeSH
Calcium saccharate tetrahydrate	MeSH
Calcium saccharate, anhydrous	MeSH
D Glucaric acid	MeSH
D Saccharic acid	MeSH
Glucarate, anhydrous calcium	MeSH
Glucarate, calcium	MeSH
Glucosaccharic acid	MeSH
L Gularic acid	MeSH
Levo gularic acid	MeSH
Levo-gularic acid	MeSH
Saccharate tetrahydrate, calcium	MeSH
Saccharate, anhydrous calcium	MeSH
Saccharate, calcium	MeSH
Tetrahydrate, calcium saccharate	MeSH
Tetrahydroxyadipic acid	MeSH
(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioate	HMDB
(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid	HMDB
D-Tetrahydroxyadipate	HMDB
D-Tetrahydroxyadipic acid	HMDB
DL-Glucaric acid	HMDB
GKR	HMDB

Molecular Formula

C₆H₁₀O₈

Average Mass

210.1388

Monoisotopic Mass

210.037567296

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1

InChI Key

DSLZVSRJTYRBFB-LLEIAEIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Fatty acyl
Fatty acid
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glucaric acid (CHEBI:16002 )
Dicarboxylic acids (LMFA01170108 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria

Biospecimen Locations

Blood
Feces
Liver
Prostate
Urine

Tissue Locations

Liver
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191961	4-trimethylaminobutyraldehyde dehydrogenase	Unknown	P49189	Homo sapiens
MMDBp0191963	Alpha-aminoadipic semialdehyde dehydrogenase	Unknown	P49419	Homo sapiens
MMDBp0191965	Aldehyde dehydrogenase, mitochondrial	Unknown	P05091	Homo sapiens
MMDBp0191966	Fatty aldehyde dehydrogenase	Unknown	P51648	Homo sapiens
MMDBp0191967	Aldehyde dehydrogenase X, mitochondrial	Unknown	P30837	Homo sapiens
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	4	Human
Bacteria	Firmicutes	1	Human feces
Bacteria	Actinobacteria	1
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	2.8	0.33			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	6526537
Human Urine	Detected and Quantified	2.9	0.2			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	6526537
Human Urine	Detected and Quantified	3.91	5.53			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	8.4		5.8	12.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	44.819	50.56			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	26.533	12.667			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.19	0.64			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.5	0.66			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.56		0.27	4.0	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	2.57	1.18			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0000663

DrugBank ID

DB03603

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16002

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Herzberg M, Tenenbaum E, Fishel B, Wiener MH: D-Glucaric acid and gamma-glutamyltransferase as indices of hepatic enzyme induction in pregnancy. Clin Chem. 1977 Mar;23(3):596-8. [PubMed:13946 ]
Matsushiro T, Suzuki N, Sato T, Maki T: Effects of diet on glucaric acid concentration in bile and the formation of calcium bilirubinate gallstones. Gastroenterology. 1977 Apr;72(4 Pt 1):630-3. [PubMed:320083 ]
Roth B, Heimann G, Gladtke E: [Excretion of D-glucaric-acid in newborns with non-hemolytic hyperbilirubinemia after phenobarbital treatment (author's transl)]. Padiatr Padol. 1977;12(4):385-93. [PubMed:904946 ]
Sorrell MF, Burnett DA, Tuma DJ, Barak AJ: Paradoxical urinary excretion of D-glucaric acid in acute viral hepatitis. Clin Pharmacol Ther. 1976 Sep;20(3):365-8. doi: 10.1002/cpt1976203365. [PubMed:954355 ]
Levy G, Khanna NN, Soda DM, Tsuzuki O, Stern L: Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion. Pediatrics. 1975 Jun;55(6):818-25. [PubMed:1134883 ]
Traeger A, Horvath T, Rechenbach C, Javor T: Beta-adrenoceptor blocking drugs and cytochrome P-450: the influence of propranolol treatment on caffeine, antipyrine, D-glucaric acid and indocyanine green elimination in patients with hepatic disorders. Int J Clin Pharmacol Res. 1986;6(3):235-9. [PubMed:3744626 ]
Marsh CA: Biosynthesis of D-glucaric acid in mammals: a free-radical mechanism? Carbohydr Res. 1986 Sep 15;153(1):119-31. doi: 10.1016/s0008-6215(00)90201-5. [PubMed:3779687 ]
Walaszek Z, Szemraj J, Narog M, Adams AK, Kilgore J, Sherman U, Hanausek M: Metabolism, uptake, and excretion of a D-glucaric acid salt and its potential use in cancer prevention. Cancer Detect Prev. 1997;21(2):178-90. [PubMed:9101079 ]
Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. [PubMed:18772850 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for D-glucarate (MMDBc0054431)

MOL for #<Metabolite:0x00007f46b7fb2390>

3D MOL for #<Metabolite:0x00007f46b7fb2390>

3D SDF for #<Metabolite:0x00007f46b7fb2390>

3D-SDF for #<Metabolite:0x00007f46b7fb2390>

PDB for #<Metabolite:0x00007f46b7fb2390>

3D PDB for #<Metabolite:0x00007f46b7fb2390>

SMILES for #<Metabolite:0x00007f46b7fb2390>

INCHI for #<Metabolite:0x00007f46b7fb2390>

Structure for #<Metabolite:0x00007f46b7fb2390>

3D Structure for #<Metabolite:0x00007f46b7fb2390>